CA2962548A1 - Composes d'enamine non cycliques pour l'absorption du rayonnement electromagnetique - Google Patents
Composes d'enamine non cycliques pour l'absorption du rayonnement electromagnetique Download PDFInfo
- Publication number
- CA2962548A1 CA2962548A1 CA2962548A CA2962548A CA2962548A1 CA 2962548 A1 CA2962548 A1 CA 2962548A1 CA 2962548 A CA2962548 A CA 2962548A CA 2962548 A CA2962548 A CA 2962548A CA 2962548 A1 CA2962548 A1 CA 2962548A1
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- Prior art keywords
- compound
- alkyl
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- substituted
- unsubstituted
- Prior art date
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- 230000005670 electromagnetic radiation Effects 0.000 title abstract description 12
- 238000010521 absorption reaction Methods 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 359
- 239000000203 mixture Substances 0.000 claims description 104
- -1 C2 to C12 alkenyl Chemical group 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000000516 sunscreening agent Substances 0.000 claims description 25
- 239000011521 glass Substances 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
- 230000000475 sunscreen effect Effects 0.000 claims description 21
- 150000001408 amides Chemical class 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 230000001681 protective effect Effects 0.000 claims description 20
- 150000002081 enamines Chemical class 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 17
- 125000003435 aroyl group Chemical group 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229920003023 plastic Polymers 0.000 claims description 12
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 12
- 229940124530 sulfonamide Drugs 0.000 claims description 12
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000008199 coating composition Substances 0.000 claims description 10
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
- 239000003599 detergent Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 5
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Chemical group 0.000 claims description 3
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical group O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical group C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical group S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 claims description 2
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- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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CN111925326B (zh) * | 2020-09-15 | 2021-11-23 | 广东药科大学 | 一种硒化异喹诺酮化合物及其制备方法和应用 |
CN113150678B (zh) * | 2021-04-29 | 2022-08-30 | 江苏利田科技有限公司 | 一种织物用肤感uv涂层剂及其制备方法 |
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US3365448A (en) * | 1964-08-11 | 1968-01-23 | Sterling Drug Inc | Acrylate derivatives |
BE793180A (fr) | 1971-12-27 | 1973-06-22 | Hoffmann La Roche | Composes utiles en fluorometrie |
EG12093A (en) * | 1975-07-03 | 1978-06-30 | Lilly Co Eli | Synthesis of 3,5 diphenyl-4-(1h)pyridazinones |
US4175087A (en) * | 1978-01-12 | 1979-11-20 | Eli Lilly And Company | α,β-Unsaturated ketones and aldehydes and method of preparation |
US4178449A (en) * | 1978-04-17 | 1979-12-11 | American Cyanamid Company | Pyrazolo[1,5-a]pyrimidines and imidazo-[1,5-a]pyrimidines |
DE2847050A1 (de) | 1978-10-28 | 1980-05-08 | Bayer Ag | Antimikrobielle mittel |
ES8104268A1 (es) * | 1979-04-05 | 1981-04-01 | Lilly Industries Ltd | Procedimiento para preparar piranonas 5-sustituidas |
US4273776A (en) | 1980-01-30 | 1981-06-16 | E. R. Squibb & Sons, Inc. | Antibacterial and antifungal derivatives of 3-(1H-imidazol-1-yl)-2-propen-1-ones |
US4663156A (en) | 1982-05-05 | 1987-05-05 | Johnson & Johnson Baby Products Company | Sunscreen compositions |
IT1161237B (it) * | 1983-04-26 | 1987-03-18 | Montedison Spa | 1,4-dichetoni-insaturi ad attivita' fungicida |
DE3825382A1 (de) * | 1987-07-29 | 1989-02-09 | Ciba Geigy Ag | N-substituierte 2-aminovinylverbindungen, deren herstellung und deren verwendung als lichtschutzmittel |
US5637718A (en) * | 1989-02-23 | 1997-06-10 | Ici Australia Operations Proprietary Ltd. | UV-absorbing compounds |
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DE19519709A1 (de) * | 1995-05-30 | 1996-12-05 | Agfa Gevaert Ag | Verfahren zur Herstellung eines chromogen entwickelten farbfotografischen Bildes unter Verwendung einer Verbindung, die mit primären aromatischen Aminen zu reagieren vermag |
JPH0952815A (ja) | 1995-08-10 | 1997-02-25 | Marine Bio Kk | 化粧品用紫外線遮蔽剤 |
DE19539623A1 (de) * | 1995-10-16 | 1997-04-17 | Haarmann & Reimer Gmbh | Sulfonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber |
DE19712033A1 (de) | 1997-03-21 | 1998-09-24 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
ES2246501T3 (es) * | 1996-11-29 | 2006-02-16 | Basf Aktiengesellschaft | Preparados cosmeticos y farmaceuticos que contienen filtros uv-a fotoestables. |
JP4205430B2 (ja) | 2001-03-26 | 2009-01-07 | ノバルティス アクチエンゲゼルシャフト | 疼痛を治療するための、バニロイド受容体アンタゴニストとして、使用するための縮合ピリジン誘導体 |
TWI316055B (fr) | 2001-04-26 | 2009-10-21 | Nippon Shinyaku Co Ltd | |
JP2003186140A (ja) | 2001-12-14 | 2003-07-03 | Konica Corp | 熱現像感光材料 |
DE10219433A1 (de) | 2002-05-02 | 2003-11-20 | Symrise Gmbh & Co Kg | Lichtschutzzubereitungen unter Verwendung von Acrylnitril-Derivaten |
JP2006257079A (ja) | 2005-02-17 | 2006-09-28 | Takeda Chem Ind Ltd | ピペリジノン化合物の製造法および製造中間体 |
CA2892395A1 (fr) * | 2012-11-27 | 2014-06-05 | Coral Sunscreen Pty Ltd | Synthese de composes absorbant les uv |
BR112016000844A8 (pt) | 2013-07-15 | 2020-01-07 | Coral Sunscreen Pty Ltd | compostos absorvedores de uv, composições que compreendem os mesmos, usos destes e método de proteger uma superfície ou tecido dos raios uv |
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TW201736529A (zh) | 2017-10-16 |
BR112017008372A2 (pt) | 2017-12-19 |
AU2022201601A1 (en) | 2022-03-31 |
AU2016329043A1 (en) | 2017-07-13 |
US20180022693A1 (en) | 2018-01-25 |
SG11201702781YA (en) | 2017-07-28 |
KR20180097443A (ko) | 2018-08-31 |
CN107108429A (zh) | 2017-08-29 |
AU2022201601B2 (en) | 2024-03-07 |
CN107108429B (zh) | 2022-08-19 |
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